Ethyl orthoformate → 3-bromo-4-ethoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide

HRID 1593769Notes

Reaction equation

HRID 1593769 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH3:27])[NH2:21].[CH2:28](OC(OCC)OCC)C>C(O)(C)C>[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH3:27])[NH:21][CH:28]=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 152708853-Bromo-4-ethoxyanilineHCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

Product 1

HCID 693154653-bromo-4-ethoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamideYield 50.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (715 mg, 2.74 mmol) in 50 mL of iso-propanol was added 3-bromo-4-ethoxyaniline (586 mg, 2.71 mmol). This mixture was heated to reflux and triethylorthoformate (2.7 mL, 16.2 mmol) was added dropwise. The reaction mixture was heated at reflux overnight. The mixture was filtered while still warm and the collected white solid was washed with iso-propanol to give 666 mg of 3-bromo-4-ethoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide, mp >250° C.; MS (ES) m/z 482.0, 484.0, 486.0 (M−H)−

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux overnight
  5. filtrationThe mixture was filtered
  6. temperaturewhile still warm
  7. washthe collected white solid was washed with iso-propanol

Sources & evidence

ORD record
ord-13a1067fdff5474ea57eaeb339e3a077
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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